Methylhydrazine → HCID 10088675, compound
Reaction equation
[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[N:23]1C(=O)C2=CC=CC=C2C1=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].CNN>C(O)C>[CH2:7]([O:6][P:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine (305 mg, 647 mmol) and methylhydrazine (31.3 mg, 679 μmol) in ethanol (7 ml) was stirred at room temperature for 1.5 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1, 9:1) to afford (Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]adenine as a colourless gum (177 mg, 80%); λmax (EtOH) 260 (13,045) nm; υmax (KBr) 3320, 3175, 2980, 1645, 1595, 1325, 1295 and 1240 cm-1 ; δH [(CD3)2SO] 1.22 (6H, t, J 7 Hz, CH3), 2.95 (2H, m, CH2), 3.97 (4H, pseudo qu, J 7 Hz, CH2CH3), 4.46 (2H, t, CH2O ), 5.85 (1H, dd, J 14 Hz and 20 Hz, PCH=CH), 6.65 (1H, ddt, J 7 Hz, 14 Hz and 52Hz, PCH=CH), 7.38 (2H, br.s, NH2), 8.15 (1H, s, H-2/H-8), 8.41 (1H, s, H-2/H-8) (Found: C, 45.30; H, 5.92; N, 20.17%; M+ 341.1253. C13H20N5O4P. 0.3H2O requires C, 45.03; H, 5.96; N, 20.20%; M+ 341.1253).